


Just an Angel of Love

by allmylovesatonce



Category: Brooklyn Nine-Nine (TV)
Genre: Cupid AU, F/M
Language: English
Status: Completed
Published: 2017-01-09
Updated: 2017-04-14
Packaged: 2018-09-15 22:46:12
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 7
Words: 18,459
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9261470
Author URL: https://archiveofourown.org/users/allmylovesatonce/pseuds/allmylovesatonce
Summary: Jake Peralta is a cupid and a great one at that. He has a reputation for being the best. But for some reason, he can't bring himself to set Amy Santiago up with her perfect man.





	1. It's Hard Work Being the Best

**Author's Note:**

  * For [startofamoment](https://archiveofourown.org/users/startofamoment/gifts).



> So this is inspired by a beautiful AU post by startofamoment on tumblr! We swapped ideas about it and this started. Here's a link to the post if you want to see it!  
> http://startofamoment.tumblr.com/post/155202542176/b99-cupid-au-in-which-jake-is-amys-designated

First off, let it be known that Jake Peralta is the best cupid around. Pretty much everyone knows it. He’s just that good. He’s been working the love game for a while and he’s a pro. He can crack a case like _that_. The research stage is critical. Cupids have to really pay attention to every tiny little detail to get it right. You can’t send someone the wrong person. That’s the opposite of the goal. It’s all about finding that person who is perfect for the charge in question. Jake likes to think his charges are lucky because they have him looking out for them. He’s the best Angel of Love out there.

His success stories are legendary. And he’s not the only one who thinks so. Angels of Love from all over know that he’s great at what he does. There was of course one particular match and meet cute that left everyone stunned. And that was like a decade ago. It was not too long after he’d started as a cupid.

His charge was a largely successful doctor named Anthony who repeatedly claimed he didn’t have time for love. Silly humans. Jake had been determined to get his match to him. Jake had found the perfect woman for him. Her name was Sarah. Each time Jake sent her to him, the doctor didn’t notice her, wasn’t interested, or left before Jake could force their meeting. Jake had been getting desperate.

That was when Dr. Too-Busy-For-Love booked a flight to Chicago. Jake did what he did best, he intervened to make their meet cute happen. Suddenly the Sarah’s sister was encouraging her to fly to Chicago to get a break from work. That led her to the airport at the same time that Anthony was there. She was on an earlier flight and running late. Anthony was the type to be early for everything so he was there an extra hour early. Jake had already worked his magic to secure Sarah a back-up flight on Anthony’s flight to Chicago.

Jake sat in a chair two gates away waiting for it to happen. He was watching Anthony go about his pre-boarding routine. He had a large coffee and several newspapers. He stood up to throw away some trash. He rounded the corner and Sarah ran right into him. His coffee covered her nice white blouse. Jake felt a smile break out on his face as he watched it happen. Anthony would have to acknowledge her this time.

“I’m so sorry!” He exclaimed. “I wasn’t looking where I was going.”

She finally looked up from her stained blouse and saw the sincerity in his face. “It’s okay. I think I have a sweater in my bag I can cover this up with.”

“No, please, there’s a store over there. Let me buy you a new shirt. I feel just awful,” he insisted.

Sure enough, she accepted. They walked over to a nearby shop, chatting the whole time. He bought her a blouse and two years later an engagement ring.

That case had been hard for Jake. He whooped as he closed the file back at his desk, happy to be finished with that one. He wrote up the report, humming as he completed it. He had never felt more accomplished in his career as a cupid. That one had really taken it out of him.

“Gotta say, that was some pretty great work, Peralta,” Terry noted, strolling by his desk.

Jake smirked smugly. “Don’t I know it.”

Terry walked back and sat down in a chair next to Jake’s desk. “No, I really mean it. That was great work. You finally found the opportunity. And boy will that be one hell of a story someday,” Terry said cheerfully.

Jake crossed his arms and leaned back in his chair. He had a faint smile on his face. “Can I admit something?” Terry nodded in encouragement. “It felt really good to crack that one. Made me feel like I was actually supposed to be here.”

Terry smiled broadly. “You’re a great cupid, Jake. We’re happy to have you working with us. And the humans who don’t know you even exist are happy that you’re working with us too.”

Little did Jake know that the big victory for him would be the one that got talked about for years to come. He had no way of knowing that the case of the doctor would spur him to get more creative and better at his job. He had only hoped that one day he’d be renowned as the best cupid around. And after that case, he started to really make a name for himself.

Of course there were other cases that proved challenging too. There was always some sort of challenge. But the case of Charles Boyle was especially challenging. Jake took the case over from an old and lazy cupid. Hitchcock had really phoned it in on poor Boyle’s case. He’d sent him Eleanor. For a few years, it seemed like Charles was happy. Enter Sleepy Stu. Suddenly Charles Boyle’s case was reopened.

First Jake sent Vivian. They were both weirdly obsessed with food. And they both got way too serious way too soon. They seemed perfect for each other. Usually Jake could tell immediately if the match would stick. He could tell by the way the first date went whether or not there would be a second date or even a marriage. He was that good. However, with Boyle, he watched a bit longer. The first date went well. The second date went well. The third date went well. Jake seemed almost sure that this match would work out. But it was the part of him that was unsure that left him from closing the case and moving on. They even got engaged and Jake was still hesitant. He couldn’t legitimately explain why he felt so unsure. Until they broke up. Vivian moved to Canada and Charles was heartbroken again. And Jake? Jake felt even surer in his instincts.

Jake sent a few random people Boyle’s way to keep him occupied while he got down to business finding the actual perfect woman for Charles Boyle. It was hard for sure. Charles was a good guy. There was no denying that. But he also had a handful of traits that made him undesirable to a certain type of woman. Jake didn’t want to leave him with another Eleanor who cheated on him and broke his heart. Or another Vivian who seemed perfect but ultimately also broke his heart. No, Jake was determined to find _the_ perfect woman. After a lot of research and digging, Jake found her. Genevieve Mirren-Carter was newly single and just as delightfully weird. She was perfect.

Jake sat invisibly on the bench next to Boyle in the courthouse. He wanted a front row seat for this. He was ready to watch Boyle meet the woman of his dreams. Boyle sat there sullenly, eating something that looked like doughnuts. Jake was curious and figured Boyle wouldn’t miss one. He snuck one out of the bag while Boyle was chewing his own. Jake bit into it but was sadly mistaken. They were not doughnuts, not at all. He spit it out in his hand and looked for a place to throw it away. He almost missed Genevieve walking toward Charles.

“Is that takoyaki?” She asked hesitantly.

Boyle looked up, clearly surprised anyone was speaking to him. He offered her some and they struck up a conversation. Instantly they started comparing all the things they had in common, starting with the takoyaki, ending with sleeping on the floor because of their dogs. That was when Charles chickened out. He quickly dismissed himself and sat back down nervously on the bench. Genevieve awkwardly walked back to where she was.

Jake groaned. He was not going to let these two weirdos not end up together. He took fate into his own hands. He grabbed one of the gross balls from Charles’s bag and chucked it in Genevieve’s direction. It hit her squarely in the back of her head. She turned around and saw Charles still staring after her. She walked back over.

“Did you throw that at me?” She accused him. Jake felt bad, but he was making magic happen.

“What? No,” Charles insisted. Luckily for Jake, Charles’s face already betrayed his nerves. Genevieve didn’t really believe him. But her walking back over gave Charles the courage to ask her to eat with him. He held out the bag and invited her to join him. Jake jumped up and she sat down where he had just vacated next to Charles. “I’m sorry for earlier. You just seem so perfect. You eat octopus balls and you sleep on the floor. I was just nervous.”

Genevieve laughed nervously. They started happily chatting again. Everything was going perfectly according to plan. Jake leaned against the wall and nodded happily. Another job well done. Another happy couple. Granted, Jake had to stay close by and observe when Genevieve got put in prison for a crime she didn’t commit. Luckily Charles Boyle was a detective. And luckily he enlisted the help of a gorgeous, smart detective that worked with Charles to clear Genevieve’s name. She was released from prison and they started their lives together.

Jake sighed as he closed the case on Charles Boyle. Soon another case slid across his desk. He opened the file and saw the gorgeous, smart detective’s face smiling up at him. Amy Santiago was his next charge.


	2. Love is Confusing Work

**Notes for the Chapter:**

> I'm sorry that it's taken me so long to update this! Part of it was writer's block but most of it was having to study for these pesky licensing exams I have coming up. I hope that this chapter was worth the wait! Thanks for all the comments and kudos! They've been greatly appreciated!

Jake felt like he spent hours poring over Amy’s file. He didn’t think he’d ever received a charge as interesting and intriguing as Amy Santiago. As he read through her file, he couldn’t help but want to meet her. She seemed that awesome. The more he read about her, the more intrigued he was.

Before he knew it, the other cupids were leaving the office.  Jake looked up, shocked that so much time had passed as he’d delved into his new case.

“You heading home?” Terry asked him as he passed by Jake’s desk.

Jake looked up at his fellow cupid. “Nope. Still got some more work to do.”

Terry chuckled and shook his head, “Man, you really do go hard on a case.”

“I’ve got a reputation to uphold, Terry,” Jake joked.

As Terry left, Jake looked over at his notes. He’d easily taken a page of notes theorizing the perfect match for Amy. It didn’t seem like enough though. The research stage is the most important part. Jake can usually start and finish the research stage in a day or two. Do a little theorizing based on their file and then doing some observation to figure out what they’re really like. While it’s important, it’s always been easy for Jake. Looking down at Amy’s file though, Jake could feel that this one was different. He knew that one or two days wouldn’t be enough to know the perfect match for Amy Santiago. This was going to take a lot of time and effort. For some reason he couldn’t name yet, he was more serious about this case than almost any other case he’d worked before.

He spent a few more hours at his desk, trying to find even the tiniest detail that would help paint the picture of Amy. Tomorrow was observation day.

Jake went to the Ninety-Ninth Precinct in New York City to start his day. He’d been there before to observe Charles. He’d spent a while observing Charles and basically already knew the best vantage points to avoid running into people. Granted, he was invisible. But still, people freaked out if they walked into something solid in the middle of an empty room. He’d learned that the hard way as a rookie.

He got there at 9:00 according to the clock on the wall. He was pretty proud of himself for getting there on time. Of course though, Amy was already there. She sat at her neat desk, already hard at work. Jake smiled to himself. He walked over and stood near her desk, observing the contents. It was basically empty. She had what he guessed was the approved amount of personal belongings on her desk. Everything was clean and pristine. He shook his head and grinned. She looked over and he could almost swear she was looking at him. He had seen her before when he was observing Charles, but he couldn’t get over how beautiful she was. She was truly breathtaking.

And as he observed her going about her life, she only got more breathtaking from there. It wasn’t just her beauty, it was everything about her. The way she held herself with the utmost composure. The way she talked with her friends animatedly, sharing her stories with them. The way her nervous tics presented themselves when she was working on a difficult case. The way she ran after and took down perps. Jake had followed her out on the job, becoming thoroughly impressed with the way she threw around a 300 pound man as if he was nothing. She cuffed him and threw him in the back of her cop car and Jake was in awe.

After three days, he knew he’d been spending too long on the research phase. But he couldn’t help it. No matter how much he learned about Amy, it never seemed to be enough. There was always some new facet of herself that she revealed throughout the time he was observing. He was so taken by how amazing she was. And he didn’t know what to do about it. She was his ultimate challenge. There was no way he’d find a match for someone as perfect as Amy. There was no man out there seemingly worthy of her. Worthy of her quirks and her laugh. Of her fears and her nerves. Of her beauty and her brains. Of her dedication and determination. No one out there was good enough for her. And he knew, he’d looked.

It was over a week later and Jake still didn’t feel ready to move on to the matching stage. He knew what he had to do. Cupids were only allowed to use it in cases of emergency. And this felt like an emergency. Cupids were normally invisible to humans. They took up space in the world, but invisibly. They were only supposed to be on earth to observe their charges in order to make appropriate matches. Still, some cases grew difficult and cupids had to intercede. So in times like these, cupids could make themselves corporeal and interact with the human world. They could meet their charges to hopefully learn what they needed to know in order to find the perfect match.

Jake had only ever humanized himself twice before. And boy had those been desperate times. Still, he’d never felt as desperate as he did now. He needed to meet Amy. Meeting her might give him some insight into her and what she found perfect in a match. He didn’t want to let her down and send her someone crappy.

She was in a coffee shop and he figured that would be a better place to meet than a police precinct. He didn’t want her thinking he was some criminal. He felt nervous for some reason. He looked down and his palms were sweating. He’d never felt like this before. He didn’t understand. Why was he so nervous about a charge? He was Jake freaking Peralta, a legend among the cupid community. He shouldn’t be nervous to do his job.

He looked in the window of the coffee shop and saw her. She was sitting reading a book. She looked calm and content. He contemplated abandoning his mission. Maybe he could find her the perfect match without meeting her. He looked back at her and noted that a sad look had crossed her face. His mind was made up. He stepped into the alley next to the coffee shop, snapped his fingers, and entered the human world.

He walked into the coffee shop and placed his order. It was surreal actually interacting with humans. People walked around him rather than him jumping out of their way. One man nodded at him as he walked by. Jake had to admit, he liked being in the world of humans. It was nice having people know he existed. He waited over by the creamer for his order to be ready. He made sure it tasted as little like coffee as possible.

He was looking at a flyer on a bulletin board when he heard his name called. He turned to walk toward the counter when someone walked right into him, spilling coffee all over his shirt. He looked at his shirt before looking up at the coffee spiller. It was Amy. “Oh my God!” she yelped. “I am so sorry!” She grabbed some napkins and started dabbing desperately at his shirt.

He started laughing. “Don’t worry about it. It’s fine,” he assured her. She looked up at him and yet again he was blown away. He’d imagined what it would be like for her to actually look at him and not through him. He could never have prepared himself for how it felt to have the weight of Amy Santiago’s gaze on him. He almost felt weightless.

She looked back at the stain on his shirt. “No it’s not. I should have been looking where I was going. I’m really so sorry.”

Jake waved it off. “Really, I promise you this shirt is not worth that much,” he said with a laugh.

“Let me buy you a new shirt, please. There’s a Macy’s right across the street. It’s the least I can do,” she pleaded.

“Second call, order for Jake,” the barista called.

Jake pointed to the counter. “That’s me,” he said, scooting past Amy. She turned to let him past, following him to the counter. He was surprised when he turned around and she was still there.

“So Jake, how bout that shirt?” She said with a guilty grin. He must have looked confused. “I heard her call your name. I’m Amy, by the way. Amy the klutzy coffee spiller.”

Jake laughed, holding out his hand, “It’s nice to meet you Amy. I’m Jake. But you already knew that.” She smiled and met his shake. “Wow, your handshake is quite firm.”

“I took a seminar,” she replied proudly.

Jake laughed and followed her out of the coffee shop and across the street to the Macy’s so she could buy him a new shirt. He almost had a sense of déjà vu. She was holding up a plaid shirt in front of him when he realized why this seemed familiar. It was the airport meet cute all over again. He was puzzled by how it had happened. He looked at Amy. Had they just had their own meet cute? That wasn’t how it was supposed to happen.

By the time he de-humanized and got back to the office, he realized his purpose for meeting Amy had been completely abandoned. They’d chatted, sure. But he seemed so stuck in his own mind that he wasn’t sure he really got the answers he needed. He’d had a fantastic time with Amy. One thing was for sure, Amy was even more amazing in person than she was on paper.

Jake was sitting at his desk, dazed by the events of his day. He didn’t even hear Rosa walk toward him until she kicked the side of his desk. His head snapped in her direction. “Well you seem deep in thought,” she said dryly.

Jake shook his head. “Just going over the events of the day. That’s all.”

“What happened?” Rosa asked, sitting down in the chair next to his desk. Jake told Rosa about how he’d met Amy so he could get more information to find her perfect match. He kept things short. He didn’t want to include all the confusing feelings that had sprung up inside him today. When he finished his story, Rosa chuckled. He gave her a look. She stood up to leave. “Sounds like some lame meet cute you’d set up for your charge to meet their perfect match.”

Jake laughed with her as she left. But then a new question arose in his head. He’d spent so much time on the research and observation phase for Amy. He could never pin down the perfect match for her. He could usually do that quickly. Maybe he couldn’t think of the perfect match for Amy because _he_ was the perfect match for Amy.

He scoffed to himself. “That’s crazy,” he muttered under his breath. He packed up his things and went home.

He couldn’t sleep that night. He just laid there replaying the few hours he’d ended up spending with Amy. He replayed the way she laughed at his jokes. He replayed the way it felt when she grabbed his arm to make him cross the street with her. He replayed the spark in her eyes as they talked. He’d seen it before… but only in his pairings. He sat up in bed, his mind wandering. Thinking out loud, he asked himself, “Could we be the perfect match?”  

**Notes for the Chapter:**

> I hope you enjoyed this! I sadly, will probably not be able to update again for a few weeks. Who knows though? Maybe I could have another sick day like I did today and I'll get to write more!   
> Please let me know what you thought or liked! I love hearing from y'all!


	3. With You, I Feel Butterflies

**Notes for the Chapter:**

> Given that it's Valentine's Day, it felt like the opportune time to update my Cupid AU. I may have put off studying to do some writing, but it'll all be okay, right? Right?

One week later, Jake found himself sitting in the coffee shop again. He was reading a book and drinking his coffee. He was also waiting for Amy to show up. The last time he’d seen her, she’d coyly said that she stopped through there every Wednesday. She’d winked at him and he knew exactly what she was trying to say to him. He hadn’t observed her in the week that had passed. Another case had come across his desk and he’d been trying to work on that too. The problem was, no matter how hard he tried to focus on his new charge, he couldn’t take his mind off of Amy.

He hadn’t seen her in a week and he was getting excited at the prospect of seeing her. They hadn’t made plans to see each other again, but Jake could read humans pretty well and he knew what Amy had meant with her wink. He wasn’t there more than ten minutes when Amy walked in. She looked especially beautiful. She saw him and met his gaze, breaking into a large smile. He smiled back, his heart beating a mile a minute. She walked past him to the counter and he went back to reading his book. Well not really reading, it was basically for show.

After a few minutes spent spiraling inside his head, he heard a sweet voice ask, “Excuse me, is this seat taken?” He looked up and saw Amy smiling down at him.

He gestured to the open seat happily. “Actually it is,” he said. She frowned, nodding slightly starting to back away. “By you,” he replied quickly, finishing his lame joke. She turned around and laughed lightly, sitting down quickly in the chair.

“Oh good! That would have been so embarrassing,” Amy mused. She laughed to herself, looking relieved. “So what are you reading?” she asked, gesturing toward his book.

He looked down at his book and back at her. “Okay, you can’t judge me.” She nodded. He held up his book. “It’s The Notebook.” She threw her head back in laughter. “You said you wouldn’t judge me!” he whined.

“I said I wouldn’t judge you. I never said anything about not laughing at you,” Amy answered.

“Whatever, my friend Terry highly recommended it,” he said defensively.

“Terry, your female friend or Terry, your male friend?” Amy asked skeptically.

“He is in fact a male,” Jake replied with a grin. “And for the record, it’s really good.”

“Oh yeah?” Amy asked, laughing. “And how many times have you cried?”

He stared at her. “I’d rather not say…” She burst out laughing again. He couldn’t help but marvel at her beauty as she closed her eyes in laughter.

“Is it actually any good? I’ve only seen the movie,” she asked sincerely.

“Umm, yeah, it is actually pretty good,” Jake said sheepishly.

They laughed together and kept talking. Before Jake knew it, it was an hour and a half later when Amy checked her phone. “Dang, they need me at work,” she said with a sigh. She looked up at him with a regretful expression. “This was fun.” Jake nodded in agreement. “Maybe we should do this again next week?”

Jake smiled in reply, “I think that sounds fun.”

“Great!” Amy said happily. “I’ll see you then.”

Jake sat there for a while longer, a pleasant feeling washing over him. He knew what he was doing was wrong but he couldn’t care. He enjoyed spending time with Amy. He knew he should be finding her perfect match, but right now he hated his job. He hated that he was an angel of love. He hated that he had to set up the woman of his dreams with another man. He hated that he was an angel of love who couldn’t find love for himself.

He’d been a Cupid for over a decade and never before had he hated it so much.

After a while more of sulking, Jake dehumanized and returned to work.

He had barely sat back down at his desk when his boss, Captain Holt, approached him. “Peralta, where are you with the Santiago case?”

Jake stiffened. He looked his boss in the eye, quickly formulating a believable lie. “Well sir, she’s been difficult so far.” Holt looked at him skeptically. “She’s one of those work before love types. It’s taking a while to really make sure I’ve got the right match. But I think I’m close,” Jake replied.

Holt nodded. “Good to hear. I trust that you’re the one for this case. Your record speaks for itself. Just remember, we as cupids don’t keep people waiting.”

“Hear you loud and clear, sir,” Jake answered. He watched as Holt left. He sighed to himself. He was breaking just about every rule in the book. He shouldn’t be interacting with Amy. He shouldn’t be daydreaming about being her perfect match. He shouldn’t be making plans to meet up with her in a week. He shouldn’t be putting off the biggest part of his job. He shouldn’t be fabricating lies for his boss. Jake couldn’t help it though, he was falling. Either in love or in a pit of despair; he didn’t know which for sure. Maybe both.

<3 <3

Amy strolled into work after leaving the coffee shop. She was visibly happier than usual. Amy loved her job, but sometimes it took its toll. Over the last week though, she’d felt lighter than usual. She couldn’t explain it. And today she felt the lightest and happiest she’d felt in a long time. It didn’t take long for people to notice.

Charles quickly came bouncing up to her as she sat down at her desk. “You seem perky today. What’s up?”

Amy smiled and shrugged it off. “Nothing new. Just happy to start another day. Not everyone gets that privilege.”

“Eww,” Gina exclaimed from the desk behind Amy. “What gross crap are you spouting, Santiago?”

Amy turned around and glared at Gina. “I can’t just be in a good mood without any real reason?”

“No,” Gina and Charles stated at the same time.

“Well I am. I just have been having a good day,” Amy maintained. She noticed Gina and Charles looking skeptically at each other out of the corner of her eye. She refused to really divulge why she was having a good day though. It was too complicated to explain to them. She’d rather just keep the feeling of it to herself.

She couldn’t really explain to herself, let alone anyone else, why a simple interaction with someone left her so giddy. Jake was really sweet. He’d had no problem with the fact that when they met she spilled coffee all over him. He even tried to pay when she demanded she was going to buy him a new shirt. They’d talked for a long time that day and she’d almost felt smitten. She’d casually mentioned that she goes to the coffee shop every Wednesday. She hoped he’d take it for what it was, an invitation. She was determined to not change her schedule to see if he was there. She always started work in the afternoon on Wednesday so she could take her time in the mornings. There was something about relaxing in a coffee shop that really made her feel at peace before heading to the hectic precinct. Last Wednesday when she met Jake, she’d gotten carried away and actually been late to work. She’d lied and come up with a good excuse and no one really cared. So today, she was more aware of the time.

She’d chastised herself for getting her hopes up that the random stranger she’d met a week before would be there again. Every time her mind went to Jake, she told herself that she was going to the coffee shop to get coffee. That was it. But when she walked in and saw Jake sitting there, she could feel the butterflies in her stomach taking flight. She couldn’t contain her smile when he looked over at her. It was all she could do to walk past him toward the counter. When he joked about the chair being taken, her heart sank at first. She had never been around someone who made her feel the way he did. He was just fun to be around and also incredibly sweet.

She didn’t know how to explain it to anyone so she didn’t even try. Maybe sometime she’d have a better idea of what was going on in her head. As it was, she couldn’t wait for it to be next Wednesday.

<3 <3

Jake walked back into the office after his third meet up with Amy. His mind was completely on her. He missed the hubbub of the cupid office. He missed the stressed looks on other people’s faces. He missed the concerned expression as his boss observed him walking back to his desk. He missed it all.

That is until Rosa came in and snapped him back to reality. “So where are you with your case?”

Jake looked up, clearly startled. “Huh?”

“Your Santiago case? You’ve been spending a long time on it,” she explained.

“I just want to make sure I’m right,” Jake defended.

Rosa glared at him. “You’ve spent weeks, if not a month or more on this singular case. You solved the Gregson case in less than a week.”

“What can I say? Santiago is difficult to pin down,” Jake lied.

“I think you’re getting up in your head,” Rosa countered. Jake looked at her thoughtfully. “I think you get caught up in your reputation and sometimes you get scared to make a move because you don’t want it to be the wrong one.”

Jake thought Rosa had a point. And on any other case, that would probably be the answer. She couldn’t have any idea how wrong she was about this particular case though. No cupid could imagine how wrong she was. He’d fallen for his charge. It was the worst case imaginable. “You might be right,” Jake offered after a minute.

Rosa nodded. “Just send the guy. You’ll feel better once you see them together.” She stared at him pointedly before walking back to her desk.

“I seriously doubt that,” Jake muttered to himself. He hated himself for it, but there was no way he was sending the _right_ guy. But Rosa had a point. Jake needed to keep up appearances. But that didn’t mean he couldn’t send a terrible match for Amy.

Jake did some research and by the end of the week Amy had agreed to go out on a date with her aunt’s dentist. He felt terrible, of course. But as he watched invisibly from the window, he couldn’t help but feel a bit gleeful that she looked miserable.

It was official. He was the worst cupid ever.

**Notes for the Chapter:**

> I still have a lot more planned for this one. I'd love to hear what you thought of this new chapter!   
> Thank you for all the comments and kudos! Y'all are the best!


	4. Fancy Seeing You

**Notes for the Chapter:**

> I didn't expect to get the next chapter written this fast. Thankfully I had an unexpected 2 hour break in the middle of my day so I got down to some serious writing!

Amy never mentioned her date to Jake. And obviously, Jake wasn’t going to bring it up. They still met every Wednesday. Neither one ever pushed it to be more than that. With Amy’s complicated romantic past (that Jake just happened to know everything about), he didn’t blame her for not wanting to really push things with him. And since he was already breaking every rule set for him, he couldn’t really push it further either. So they met for coffee on Wednesdays before Amy had to be at work. They’d chat and laugh and Jake would fall harder for her.

Jake walked into the coffee shop and Amy immediately jumped up at him. He stumbled back in shock. “Hi,” he said in a daze.

“Hi,” she said quickly. “Okay, so I have to run by work really quick to sign a form that I must have forgotten last night. They need it before I normally go in.”

Jake felt disappointed. “Oh, okay.”

Amy dipped her head slightly as if she was debating what to say next. “Well, I mean I still don’t have to go to work until my normal time. So I could just go there and come back. I didn’t want you to think I didn’t come today.”

Jake nodded in understanding. “Do what you have to do.”

Amy paused, looking at Jake carefully. “I mean if you wanted to, you could go there with me. I’m not going to be there too long.”

Jake smiled broadly. “That sounds good. It would be cool to see a police precinct.”

Amy bounced happily on the balls of her feet. “Great! Let’s go!” she exclaimed, grabbing his hand and leading him out of the coffee shop. He looked down at their joined hands as she led him through the busy New York streets. The precinct was not too far from the coffee shop. When they got there, she released his hand. His stomach sank a bit at the action.

“I promise this will just take a minute,” Amy said as they stepped into the elevator. Jake had, of course, been to the precinct before when he was observing both Amy and Charles. It was completely different being there with Amy. He could take in so much more about the place. He’d never noticed so many other people. He knew he really zeroed in on people when he was in observation mode, but he didn’t realize how much he actually missed.

Amy strode out of the elevator and straight for her desk. Jake followed her. He was still pretty zeroed in on her. He always was. She was rifling through papers when he heard his name.

“Jake?” He whipped his head in the direction of the speaker. Amy was the only human who knew his name. He saw her standing in the doorway, frozen.

“Gina?” He asked incredulously.

Amy looked over at him. “Oh, do you know Gina?”

Jake nodded nervously as he saw Gina slowly walking closer to them. “Yeah, uh, Gina and I go way back.”

“Huh, small world, I guess,” Amy chuckled. “Gina, this is the Jake I mentioned.”

Jake couldn’t help but feel happy at the fact that Amy had mentioned him to her friends. Gina nodded as she approached them. “Jake, long time no see.”

Jake swallowed nervously. They were so close to blowing everything. “Yeah, how’ve you been?”

Amy was still rifling through papers on her desk, oblivious to their weirdness. “Amy, Charles has the form you need in the briefing room.” Amy released an “ah” and went to find Charles. Gina grabbed Jake’s arm and led him away from Amy’s desk. She led him to a closet and shoved him in.

“What are you doing here, Jake?” she questioned.

Jake shrugged. “I’m here on work.”

“Then why can I see you?” Gina interrogated.

“I…humanized…” Jake replied, feeling like Gina should know how she could see him.

“Not what I meant, Jake. Is Amy your charge?” He nodded in reply. She stared at him for a minute. “You’re not working.”

“What? Yes, I am,” he insisted.

“No. I know you Jake. You never need to humanize. Unless your skills as a cupid have considerably decreased in the last few years. You always bragged that you didn’t need that ability. That you were too good without it. So which is it?”

“What can I say? Amy’s a hard case,” Jake offered.

Gina threw her head back in laughter. “Like hell she is. I could have matched her perfectly the first day I met her. You don’t need to humanize to crack Amy Santiago.” Jake’s face fell. “What are you really doing here, Jake? Why are you with Amy?”

“I…uh,” Jake faltered.

Awareness dawned on Gina’s face. “You love her. You fell in love with your charge.” Jake couldn’t even try lying. He nodded once. She sighed. “And now you’re breaking all the rules to try and spend time with her.” Jake nodded again. Gina shook her head. Suddenly she reached out and slapped the side of his head. “Boy, what kind of idiot are you?”

“What?” He exclaimed, shielding himself from her slaps.

“Do you want to get your wings clipped like I did? Breaking the rules is dumb, Jake,” Gina insisted. “And believe me, I know Amy. She’s not worth it.”

Jake shook his head. “I think if it came to that she might be.”

“That doesn’t mean you’re her match, Jake. And it’s selfish of you to keep her from him. Isn’t that the Cupid crap we all used to spout?” she asked. “Jake, don’t throw everything away for one person. You may think you’re above the rules, but you’re not. Don’t do it. It’s a lonely life with clipped wings,” Gina said sadly.

“You miss Rosa?” Jake asked hesitantly.

“Don’t,” Gina warned, pointing a finger at him.

“Are you really that miserable?” he asked.

“I mean, human life is okay. I have a job and other cool stuff going on in my life, but it’s not the same. I trained to be a cupid and I failed. And every morning when I wake up as a human, that’s what I think about. Is that what you want?”

He paused, thinking things over. What Gina described sounded sad. But she was right about one thing, he did love Amy. There was no denying it at this point. “I don’t know,” he said.

“Whatever, Jake, it’s your call,” Gina surrendered. “But you know, if you get your wings clipped and live life as a human, someone else is going to take over Amy’s case. And how will you feel when she meets her perfect match and you broke all the rules for nothing?”

Jake froze. She was right. She opened the door and started to leave. “And for what it’s worth?” she started. He looked up at her. “Yes, I do miss Rosa. Every day.”

She started to walk away. “Hey, Gina,” he called, following after her. She turned back to look at him. “She’d never admit it, but I know she misses you too.” Gina smiled sadly and walked back to the bullpen.

Jake followed her and found Amy waiting for him. “You ready to go?” she asked.

Jake made eye contact with Gina. She gave him a warning glance. He looked back at Amy. “Yeah. Let’s go.”

<3 <3

He heard a knock at his door so he jumped up from his chair. He opened the door to see Rosa standing there. “Rosa! Thank you for coming.”

Rosa nodded and walked in as Jake closed the door behind her, looking around the hall suspiciously before actually shutting the door.

“What do you want?” Rosa asked blankly.

“I messed up. I messed up badly,” Jake explained.

Rosa furrowed her brow. “What did you do?”

“Before we talk about what I did wrong, let’s reflect on our long standing friendship,” Jake said, trying to buy himself some time before Rosa’s judgment came rolling in. She glared at him. “Remember what it was like going through school trying to decide what you want to be? Remember when we both admitted we had been torn between being a cupid and a guardian angel?” Rosa continued glaring. “Sometimes I wonder what my life would have been like if I’d gone the guardian angel route. It always seemed so cool when we were in school. But ultimately I was drawn to being a cupid. Something about making other people happy just drew me in. You know?” Rosa shrugged. “I didn’t think I’d ever get to a point in my career where I didn’t want to do this anymore.”

Rosa looked confused. “Jake, what are you talking about?”

“When we met at the Cupid Academy, we were so full of hope and dreams,” Jake mused. Rosa looked skeptical. “Okay, maybe it was just me. But what happened to that? We seem so jaded now.”

“That’s life, man. It’s not always going to be what you want,” Rosa reminded him. “But you’re still good at your job. You don’t show that you feel jaded.”

Jake sighed. “Yeah, well that’s more recent.”

“It’s this Santiago case, isn’t it?” Rosa asked knowingly. Jake broke eye contact with her. “What is it with this case? It’s been months. How is it this hard for you to find her match?”

Jake sat down on his coffee table. He sighed, looking down at his hands. “I fell in love with her,” he confessed.

“What? How?” Rosa demanded.

Jake couldn’t look at her. “Well, it started just by looking at her file. And then I got in deeper and it got worse.”

“Is that where you go all the time?” Rosa asked. “Are you observing her all the time? One sided love is not the same as real love, Jake.”

“That’s the thing, I don’t think it is one sided,” Jake confessed.

Rosa looked confused. “How would it not be one sided?” Jake swallowed harshly, avoiding all eye contact. Rosa put it together. “You met her. You humanized and met her.” Jake nodded guiltily. “You really think she’s in love with you after one time?”

Jake looked back up hesitantly, afraid to say the next part. “That’s the thing, Rosa. It hasn’t just been one time.”

Rosa sat down on one of his chairs. She was silent for a long time. “How many times has it been?”

Jake shrugged. “At least once a week for a couple months…”

Rosa shook her head. “Jake, what were you thinking?”

“I don’t know, Rosa. I guess I wasn’t.” He sighed. “I think it’s true what humans say. You lose your head when you’re in love.”

Rosa glared at him. “Still, you should have known better, Jake. What if Holt found out about this?”

“I know,” Jake admitted. “That’s why I came to you. I need your help. I don’t know how to call it off but Gina told me I had to.”

Rosa visibly stiffened. “Gina? You saw Gina?”

Jake froze. “Oh crap. I wasn’t gonna mention that. But yeah, she works with Amy and I ran into her.”

Rosa nodded curtly. “Good for you.” She paused. “Why did she say you had to call it off?”

Jake didn’t want Rosa to know everything that Gina had said to him. He knew it would crush her. “She said she didn’t think I’d take too well to my wings being clipped. And that it would all be for nothing because Amy would just end up with someone else.”

“She makes a good point,” Rosa commented.

“I know. But I still don’t know what to do. The idea of not seeing Amy kills me. And the idea of _me_ being the one to send her the perfect man kills me even more.”

“What, do you think you’re the perfect man for her?” Rosa asked bluntly.

“If I was a human, yeah, I might,” Jake confessed.

Rosa shook her head. “But you’re not. You’re a cupid. You have to get over this delusion, Jake. You have to do your job.” Jake knew Rosa was right. He had to let Amy go. He just had no idea how to do that. How could he let the woman he loved go?

Humans were right. Love is the worst.

**Notes for the Chapter:**

> So just to elaborate on what I kind of hinted at in this chapter, in my mind, there's another realm where Cupids live. But they aren't born Cupids. They get to go to school and choose what they want to be (kind of like us) but they have a certain amount of options like cupids or guardian angels or maybe even fairies. So Jake, Rosa, Holt, Terry, and Gina all chose to be cupids. But if you mess up, you can have your wings clipped and then you're a human.   
> I just wanted to explain the way things were set up in my mind. I hope y'all are still enjoying this!


	5. Everybody Hurts Sometimes

“Peralta! My office. Now!” Jake heard his captain yell. His hands shook as he stood up to walk to Holt’s office. He caught Rosa’s eye as he walked past her desk. She looked concerned. Jake hoped that Rosa hadn’t tattled on him. He didn’t know if he could forgive her if she’d done that. He walked into Holt’s office and closed the door behind him. Jake stood in front of his captain, ready for whatever punishment was likely coming his way.

“I’ve done some investigating, Peralta,” Holt started. Jake could feel his entire body tensing. “It has genuinely baffled me that it’s taken you _this_ long to find a suitable match for Miss Amy Santiago. So I dug a little deeper. Not only did you do way more observation than necessary, you humanized repeatedly. Peralta, you know as well as anyone else that humanizing is supposed to be a last ditch effort. It is also not supposed to happen multiple times. No one is that difficult to match. You’ve been abusing your title, Peralta. The things you have done are worthy of clipping.”

Jake closed his eyes. He could feel his stomach sinking. He was actively preparing himself for Holt to clip his wings then and there.

“However, before this, your record was basically spotless. You are one of our best cupids,” Holt continued. Jake looked at him questioningly. “Given that no one is perfect, I’ll allow you one more chance.”

“Sir –” Jake began.

“But let me assure you, that if you continue to mess around with this case rather than wrapping it up, you’ll be out of here. Your wings will be clipped and you’ll be a human,” Holt reminded him.

Jake nodded quickly. “Give me a week, tops, Sir. I can turn this around,” Jake promised.

“I believe you. But consider yourself on probation.”

Jake nodded quickly and exited the office once he was dismissed. He walked past his desk, scooping up Amy’s file and walking quickly toward another room. He couldn’t sit with everyone’s eyes on him. Not as he sat there trying to find the perfect match for the love of his life.

Thankfully, Holt had given him the week that he asked for. Normally, Jake could find a match in a day. He knew in his heart this was going to take a lot longer. He might even have to recruit Rosa.

It had been two weeks since he’d seen Amy. He was starting to lose it. The idea of never seeing her again was eating at him. He didn’t know how to wrap up this case. He only knew that his job literally depended on it.

<3 <3

“You haven’t finished this yet? What the hell, Jake?” Rosa snapped. Jake held his hands up defensively. “It’s been almost three weeks since you told me you loved her. How have you not just wrapped this up yet?”

“It’s easier said than done, Rosa,” Jake defended.

“That’s a lie. You got reprimanded from Holt. That should be enough to kick your ass in gear.”

“It clearly was. That’s why I’m pouring over this trying to find her perfect guy. But I can’t be objective. That’s why I need your help,” Jake begged.

Rosa rolled her eyes. “I should tell you no. I should just let you flounder for being so reckless.”

That’s when Jake got angry. He slapped the file down on his coffee table, standing up. “This isn’t me being reckless, Rosa. I’m in love. There’s a difference. Reckless was when Gina had to have the most dramatic meet cutes as possible and she landed her charges in the hospital. _Reckless_ was when Gina got her wings clipped because she got her last charge hit by a bus! Don’t accuse me of being reckless. I may have done some stupid things, but it was all in the name of love. And isn’t that what our damn job is all about?”

Rosa stared at him. Suddenly her face softened. “Look Jake, I have never fallen in love with one of my charges, but I’ve lost someone that I love too. And I know that it’s hard. Like impossibly hard. But sometimes you just have to rip off the band-aid and go through with it. You have to go on with your life.” She paused. She looked at Jake meaningfully. “Isn’t that what Amy would want?”

Jake scowled at her. “That’s low. What would you do if I turned the tables like that on you? What if I said that about Gina?”

Rosa chuckled. “Yeah, I’d probably punch you.” She stopped laughing and gave Jake a serious look. “But Jake, you have to do this. And I think we both know that you know who to set her up with.”

Jake looked down at the table. He looked at the faces of the men whose pictures were spread across his table. It killed him, but he knew who it was. He sighed. “Give me the Majors file.”

<3 <3

Gina watched Amy walk in, sulking more than usual. “What’s up with you?” she asked Amy.

Amy looked at her quickly before settling down at her desk. “Nothing.” Gina clearly didn’t believe her. One thing she’d retained from being a cupid was that she was still great at reading people.

Charles walked over from his desk. “No, Gina’s right. Something’s up. What’s up, Buttercup?”

“Buttercup? Really Charles?” Amy questioned. Charles shrugged. She looked over at Gina and Charles, noting their prying expressions. She rolled her eyes and moved her chair closer to Gina’s desk. Charles followed her. “I thought I’d met someone. But it turns out it was just nothing.” Gina immediately felt guilty. It wasn’t a feeling she was really used to. But she knew Amy was talking about Jake. And it had been three weeks since Gina and Jake had reunited and Gina had talked sense into Jake. Clearly he’d followed her advice and backed away from Amy.

“Why don’t you just text him? See why he stood you up,” Charles offered.

“We never exchanged numbers,” Amy explained. “We never even went on a real date. We just met at the coffee shop at the same time every Wednesday. And as silly as it was, it always made my week. He was a really great guy. But it’s been three weeks since I’ve seen him. That pretty much means it’s over, right?”

“I don’t know about that,” Charles replied, reassuringly.

Gina wrinkled her nose. “I have to agree with Amy. One time is an accident. Two times is a coincidence. But three times? Three times of missing your unofficial date seems pretty blatant.” Amy’s face fell at Gina’s evidence. “Sorry, Ames.”

Amy sighed, scooting her chair back to her desk. “It doesn’t matter anyway. Just move proof that love isn’t real.”

Gina groaned to herself. She hated knowing what she knew. She wished she’d never walked out of the briefing room in time to see Jake. As great as it had been to see her old friend, she wished more than anything to not know he actually loved Amy but couldn’t act on it. How could Gina spin that to Amy? She couldn’t. Humans didn’t know Cupids existed. So that was that.

Gina went about the rest of her day. She wouldn’t say she and Amy were best friends. Hell, sometimes she wouldn’t even really call them friends. But she still didn’t like seeing Amy like this. She seemed so defeated. Nothing seemed to cheer her up. Not even when the captain stopped by Amy’s desk to tell her that some other detective from another precinct would be working a case with Amy. Amy loved working.

Charles walked back over to Amy’s desk. “Who did he say is working a case with you?”

Amy looked at him curiously. “Detective Dave Majors. Why?”

“Dave Majors?” Charles practically squealed. Gina shook her head at him. “He’s only the best detective in the NYPD.”

“I take offense to that,” Amy replied. Gina chuckled.

“I’m serious, Amy. He’s got tons of medals because he’s made so many amazing solves on really hard cases. He’s awesome. I’ve never met him, but I just know.” Charles looked at Amy skeptically. “How do you not know who he is?”

Amy shrugged. “I don’t know. Apparently he’s supposed to be here in like five minutes.” Amy turned back to her work. Charles went back to his desk. Amy looked back at him. “Oh and Charles, please don’t ask for his autograph or anything weird like that. I’d like to not freak him out immediately.”

“Don’t worry, Ames. I’ve got a stun gun in my desk. I’ll take care of Charles,” Gina reassured her. Amy looked at her startlingly. Gina laughed. “I mean, no I don’t. What? That would be crazy.” She tried to smile at Amy convincingly as they both got back to work.

It wasn’t but a few minutes later when the elevator doors opened and a handsome, masculine man strutted into the precinct. Gina was staring at him. Gawking might be a more appropriate word, actually. He walked right over to Amy’s desk.

“Santiago?”

Amy turned and knocked a cup of pencils off her desk. The man caught it in his hands before any of them could spill to the floor. Amy’s shocked and impressed face matched Gina’s.

“Hi,” Amy said, slightly stunned.

“I’m Majors, Dave Majors,” the man replied, holding out his hand for her to shake.

Gina scoffed quietly to herself. How could this be happening to Amy Santiago? It was like a scene from a movie. With the ultimate meet cute. Gina sighed as a realization hit her. She knew someone perfect at setting up the ultimate meet cutes. And he was likely there at that moment, dying inside.

She looked around, trying to see if she could figure out where Jake was. He had to be there. He never used to miss the meet cute. For cupids it was the best part. No one was paying attention to her. She whispered to the air, “I’m sorry, Jakey.”

Soon a note appeared on her desk seemingly out of nowhere. In the chicken scratch she remembered reading years ago was simply written “Take care of her.”

**Notes for the Chapter:**

> Wow, I can't believe it took me a month to update this! Sorry, guys! I hope you enjoyed this chapter! As always, I'd love to hear your thoughts!


	6. Everybody, Everybody Wants to Love

Jake was walking, well more sulking, around the Cupid headquarters when Captain Holt stopped him. “Peralta, I need your help.” Jake lifted his eyebrows in question. “I double booked myself today. I have an important meeting and I forgot that today is the day to talk to the prospective cupids. Could you handle that for me?”

Jake was taken aback. “You want _me_ to talk to the prospective cupids? Why not Terry? Isn’t he next in command?”

Holt nodded. “He is, but he is out with the Heartbreak Detector acquiring new charges. As one of our finest cupids, I really need you to step up.”

Jake nodded. “I can do it, Captain. I’ll talk to these little dweebs.”

“Please don’t speak like that in front of them,” Holt added nervously.

“Absolutely, Sir,” Jake agreed. He watched the captain leave before he leaned against the wall and sighed. He was not in an appropriate headspace to talk up the job of Cupid. He’d gotten the notification of Amy’s first date. Usually first dates were when cupids checked back in and made sure their matches actually worked. Jake looked at the notification on his computer and immediately deleted it. He didn’t go to every first date. The ones he was the surest of, he skipped, usually to do more work. He just couldn’t force himself to go see Amy on her date. He had made up his mind. He was skipping it.

He walked into the auditorium that held easily 100 prospective cupids. He remembered this part. Usually more than half had decided to be cupids. There was always a good chunk spilt between cupids and another field. And then there were the stragglers who just had no idea what they wanted to do and came to the cupid meeting to get more information. By the time the meeting had come around for Jake, he’d fallen into the first group.

Now he stood in front of all these people and he was supposed to inspire them to become cupids. Easier said than done.

“First off, welcome! We here at the cupid headquarters are happy you’re considering becoming a cupid,” he began. He figured Holt would start with something like that. “We’re here to talk about being cupids. We’re here because you are interested in helping people find love. But what even is love?” Jake asked.

One girl in the front raised her hand. Jake shook her off.  

“Love is everything. Or so they say. It’s a feeling in your heart when you look at the person you love and you just feel warm and happy inside. It’s in your brain when you think of that person and all the reasons why you love them. It’s a reaction. It’s when you hear the person you love laughing at something you said and you feel weightless. You feel like nothing in the world even matters except this person. Captain Holt likes to say that love is like oatmeal. It sustains you. Love is a powerful thing,” Jake explained. He saw the faces of the crowd. He was nailing it.

“But love can also be destructive. It can be painful. What if that person doesn’t love you back? What if that person _can’t_ love you back? It’s hard to accept that love can bring you all the happiness in the world and also bring you unspeakable pain. It does go both ways,” Jake furthered. He noted the looks of confusion, but all he could think of was Amy. “Love is what makes people want to get up in the morning, but it can also be what makes people wish they didn’t have to be a part of the world anymore. Love is…” Jake faltered for a second. “Love is complex.”

He saw the prospective cupids looking at each other and back at him in confusion.

“There’s the song that says that love is all you need, but that’s wrong. You do need love, but you need other things too. You need timing. You need the other person to be able to love you back. You need the world to sync up and allow these two people to live and love at the same time. And that’s harder than it seems. You can have the perfect match and it goes to crap. You can watch all your hard work go down the drain. You can see the purest love be reduced to tears. The world is a hard place. Especially the human world. We may not live in it, but we dabble in it.”

Jake decided to steer away from his thoughts of Amy and attempt to give this speech some direction. “Being a cupid can be the most worthwhile job in the world. You can see how important you are in people’s lives, even if they don’t know you exist. But it isn’t without its hardships. Sometimes all you want to do is directly intervene, but you can’t. Your place is here, as a cupid. Your place is to find two lonely people and give them love. And when you get to observe that in real time, it’s truly something wonderful. You get to look at two people who are happy and know that you did that. I can’t tell you all that being a cupid is the right decision for you. It’s hard. But honestly, it’s worth it just for that moment,” Jake concluded.

The auditorium burst out in applause. Jake was definitely not expecting applause. He nodded and waved to them, a small smile crossing his face. He at least hoped Holt would be proud of him. He may have gotten side tracked, but he found his way. “Okay, thank you! Questions?” He saw at least 20 hands go up.

After he’d finished speaking with them, he ran into Rosa on the way back to his desk. “Where were you?” she asked.

“Talking to prospective cupids,” Jake explained.

“You? In this state?” Rosa questioned.

“I managed to do okay,” Jake replied. “Plus, I convinced myself of something.” Rosa furrowed her brow at him. “I’m not skipping the first date. It’s part of my job. Maybe it’ll even give me closure.”

Rosa nodded approvingly. “Good call.”

He nodded, putting on his jacket, ready to leave the office.

He found his way to the little Italian restaurant where Dave Majors was taking Amy for their first date. Jake walked in and quickly spotted them. He felt a stab in his heart as he saw her laugh at something Dave said. He remembered how it felt to be on the receiving end of that laugh. And now he was literally invisible to her. In an instant, he changed his mind. “I can’t do this,” he muttered to himself.

He walked quickly outside, stopping just past the door. He took one last look in the window next to the door. He could see a bit of Amy’s face past the other people. He reached out and touched the window. “Goodbye, Amy Santiago.”

He pushed his hands into his jacket pockets and walked away from the restaurant. He wasn’t ready to return to headquarters or to his apartment. He decided to prolong his time in the human world. As he walked, he was reminded of a bar Amy mentioned that she went to when she’d had a hard day at work. Jake figured it couldn’t hurt to try and numb the pain. He walked to the bar, humanized, ordered a drink, dehumanized, and retreated to a corner of the bar. He planned to drink his sorrows away in silence.

<3 <3

Terry rushed back into headquarters, hoping to find Rosa as quickly as possible. “Diaz!” he called.

She popped her head out from the break room. “Yeah?”

“I need your help,” Terry started, rushing towards her. He sat down in front of her. “Are you still as close with Peralta as you used to be?”

Rosa shrugged. “I guess so. Why?”

“I need to know why I found him with the Heartbreak Detector,” Terry explained.

“You did?” Rosa asked, leaning forward. “It can detect fellow cupids?”

“I’ve never had it do so before, but I guess it can if the heartbreak is profound enough,” Terry reasoned. “But what is Jake heartbroken about?” Rosa shrugged, trying to play off her knowledge. “Come on, Rosa. I know you’ve been Jake’s confidant for the last few years since Gina’s been gone. What is going on with him?”

Rosa sighed, sitting back in her chair. “Fine, but I didn’t tell you this.” Rosa proceeded to inform Terry of precisely why Jake was so heartbroken.

Terry leaned back in his chair, covering his mouth with his hands. “He fell in love with his charge?” he whispered. Rosa nodded. “I can’t believe this.” Terry’s mind was moving so fast, he could barely focus on anything. “If he’s in love with her, how do we even know this match is legit?”

“He sent her bad matches before. Holt nearly clipped his wings over this case. He set her up with a legit match. He made me check it,” Rosa proved.

“But there’s still a chance it’s wrong,” Terry replied eagerly.

Rosa stared at him, confusion written on her face. “Why do you want it to be wrong?”

“Maybe Jake’s heartbreak doesn’t have to be for nothing,” Terry  countered. Rosa gaped at him. “Look, there’s still a chance Rosa!”

“A chance for what?”

Terry smiled broadly. “For Jake to have his happy ending.”

“He’s a cupid. She’s a human. How is there a happy ending there?” Rosa demanded.

“We’ll just have to see,” Terry said cryptically. “Could you find where the date was happening? I want you to go observe. I’m going back to Jake. You tell me if the date is going well or if we still have a shot.” Rosa nodded, though she still looked rather confused. “Tell me you can do this, Rosa.”

Rosa looked up at Terry. “I can do it.”

Terry held his hand in. Rosa laid hers on top of his. “And break!” Terry yelled, lifting up their hands, and immediately running from the break room.

<3 <3

Rosa found herself at a small Italian restaurant in enough time for Amy to still be on her date. She recognized her face as she walked in. Rosa stood out of the way, still invisible to the human world. She saw the guy she and Jake had picked. He was bent over his plate, devouring whatever was in front of him. Amy was politely ignoring his demeanor. Rosa couldn’t tell yet if she was unhappy though. She needed to get closer to read the vibe of the date.

Majors was finishing some joke. “So then the banker said, “Why don’t you check your pants?” Isn’t that hilarious?” Majors asked through his laughter. Amy laughed nervously.

The waitress came by the table, clearing their plates. Rosa was starting to worry. Her time for observation was coming to a close. Just then the waitress asked, “One check or two?”

“Two,” Amy replied quickly. Too quickly. Like she wanted to beat Dave to the punch.

“Gotcha,” Rosa whispered under her breath. She didn’t wait to hear Amy’s explanation or anything. But the fact that Amy was demanding to pay for her meal was enough to tell Rosa what she needed to know.

Rosa walked out of the restaurant and pulled out her cupid-to-cupid walkie talkie. “Terry, you there?”

“I’m here,” Terry’s voice rang through the speaker.

“Are you with Jake?” Rosa asked.

“I have eyes on him, but he doesn’t know I’m here,” Terry answered.

Rosa ducked into an alley close to the restaurant. “The match isn’t good. She isn’t interested in him.”

“What? You’re sure?” Terry demanded.

“Yeah. She wouldn’t even let him pay for her meal,” Rosa confirmed.

“Oh, dang!” Terry replied. “Are you still at the restaurant?”

“I’m nearby.”

“When she leaves, give her the idea to go to a bar called The Stag’s Head,” Terry insisted.

Rosa agreed. “But what is going to happen once she gets there?”

“All I need is one minute of interaction to know what I need to know,” Terry promised.

Rosa rolled her eyes and walked back toward the restaurant. Terry better be sure about this.

<3 <3

Jake sat in his corner of solitude, still nursing the first beer he bought. He wanted to drink to forget but he didn’t want to have to humanize to get more drinks. He just wanted to sit there and hate life for a bit longer. He was a joke. An angel of love who couldn’t find love for himself. They should make a movie of him.

He knew cupids that had married. Holt was married. Terry was married. He’d never really been invested in his own love life. And then Amy’s file came across his desk. Looking back, he didn’t really get how he fell so hard so fast. Though he guessed that was just how love worked. Sometimes it was confusing.

More than anything, he wished he’d gotten the chance to say goodbye to her. He’d missed their unofficial date three times now with no explanation. He knew she had to be at least somewhat hurt by that.

Or maybe he was overestimating how much he meant to her.

He was ignoring the groups of happy people in clumps all over the bar. He was fine to sit in solitude and not interact with anyone. That was when he heard someone approach him.

“Hey there, Stranger,” a familiar voice said.

Jake whipped his head to his left to see Amy standing in front of him, a nervous smile on her face. Jake looked around quickly. He hadn’t humanized. How could she see him? “You can see me?” he asked stupidly.

She chuckled. “Yes. You must have forgotten your Invisibility Cloak at home.” Jake laughed. He still didn’t understand how he was suddenly visible. “So what brings you here?” Amy asked softly.

“Uh, I remembered that you said you came here after hard days at work. So that was kinda why I was here,” Jake explained. He motioned to the seat across from him. “Would you want to sit?”

Amy looked at the seat and then back at Jake. She shrugged and sat down. “I haven’t seen you in a while.”

Jake looked down at his beer, nodding solemnly. “Yeah, I’m really sorry about that. Do you want to hear my crappy, fake excuse?”

Amy smirked. “Try me.”

Jake sat a little straighter, looking her in the eye this time. “Work has been crazy lately. I couldn’t get away.” It wasn’t a total lie.

Amy scrunched her nose. “Didn’t you say you worked for an online matchmaking site?”

“Umm, yeah. What can I say? E-harmony is kicking our asses,” he joked. Amy laughed at his joke. The feeling of weightlessness returned. He still didn’t understand how this could be happening. “What brings you here?” Jake inquired. Last he’d seen her, she was on a date. “You look really pretty, by the way,” he added.

She smiled brightly at him, looking down at her dress. “I was on a date.”

“Oh,” Jake said simply, paying real attention to his beer. “How was that?”

“Well it’s 8:30 and I’m at a bar by myself. You tell me,” Amy answered. Jake looked up at her. He was confused. Her date should have gone perfectly. He was supposed to be the perfect match for her. Jake was never wrong.

“I’m sorry. What happened?” Jake inquired.

Amy shrugged. “Not really much of anything. He was a nice guy. Seemed perfect on paper, but we just didn’t _click_. You know?”

Jake tried to fight a smile. He didn’t know how successful he actually was. He nodded his head. “Yeah, that’s the worst.”

Amy nodded in agreement. “It is. It was an okay meal, but shouldn’t it be better than okay? I mean I felt like I just sat there comparing him to…other guys,” she finished after a pause. Jake fought the urge to evaluate what the pause meant. Nothing had changed. He was still a cupid and she was still a human. Just because he mysteriously humanized, didn’t mean anything was different.

He was just about to speak when the bartender called out. “I have a wallet here for Jake Peralta!” Jake looked over at the bar in confusion. He never carried a wallet. If he was going to interact in the human world, he just kept a handful of cash in his pocket. He excused himself and walked toward the bar.

“Umm, I’m Jake Peralta,” he said. The bartender opened the wallet, looked at something and handed it over to Jake. He looked in the wallet at what the bartender could have seen. It was a license with Jake’s picture. Jake was taken aback at the sight of it. Behind it, there was an ATM card, a credit card, a library card, and an insurance card. Jake was baffled by the contents of the wallet. He looked in the money slot, finding multiple bills in there, but also a note.

_Jake,_

_All it took was one glance at you and Amy to know that there was something special there. Love isn’t something we should fight and agonize over. It’s something we should embrace. So I’m helping you embrace it._

_You’ve been a remarkable cupid over the last decade. You’ve helped thousands of people find love. Now it’s time for you to find it for yourself. And you have. There shouldn’t be anything stopping you from being with your love. So now there isn’t._

_Your wings have been clipped! Don’t freak out; it’s honorable clipping. You served your cupids well. So now go live your second life, your human life. Live it with Amy and be as happy as you’ve made others all these years._

_Don’t worry, Amy’s case is closed. It’s quite clear her perfect match found her. No one will assign her another match. Captain Holt was completely on board with the idea of your honorable clipping. You deserve to be happy, Peralta._

_We’ll miss you._

_Terry_

_P.S. the rest of your new identity is waiting for you at the address on the back of this letter._

Jake felt like he had to read it a few times to really understand what happened. He looked back at Amy and she was looking over at him expectantly. He folded the letter quickly and shoved it in his pocket, strolling back over to the table.

“Everything okay?” Amy asked.

Jake was still a bit dazed, but he looked up at Amy. “Yeah, I just wanted to make sure it was all there.” Amy nodded understandingly. “Hey, I feel like I know what my answer might be, since you just were on a date and all that, but how would you like to grab a drink with me?”

Amy narrowed her eyes and stared at him. Jake could feel his palms sweating. His wings had been clipped.  What if Amy didn’t actually return his feelings? Suddenly she smirked and held her hand up for the waitress passing by. “Could I get a vodka soda and…” she looked over at Jake for him to finish.

“Uhh, same,” he added. The waitress nodded and walked toward the bar. Jake looked back at Amy. “Is it weird to say I’ve missed this?” he asked, gesturing between the two of them.

Amy smiled brightly. “No, I was actually just thinking the same thing.”

<3 <3

Gina was leaving work later than usual. She didn’t really understand how she got roped into these things, but she did. It was just after 8:00 when she finally was leaving the building. She opened the door and stopped dead in her tracks. “Rosa?” she asked with a slight gasp.

Rosa nodded at her as she leaned against one of the police cars.

“What are you doing here?” Gina asked, still standing on the stairs.

“I need to talk to you,” Rosa replied.

“I thought you said we’d never see each other again because you weren’t reckless like me and you wouldn’t just humanize to see me?” Gina reminded her bitterly.

“Well, desperate times and all that crap,” Rosa answered, moving from her place in front of the cop car. “I need to ask you something that’s kind of unfair.”

Gina stepped down onto the sidewalk. “I refuse to give you any kind of blessing with anyone else.”

Rosa shook her head. “It’s not about that.” She held out a thick envelope for Gina to take. “I need you to give this to Jake.”

“What?”

“Jake’s wings got clipped. This is the rest of his human identity. We’re trusting you to give it to him,” Rosa explained, gesturing with the envelope.

Gina stared at the envelope and back at Rosa. “What? How did Jake get his wings clipped? He called it off. I know he did. I saw the aftermath of it here. How could Holt clip his wings?”

Rosa shook her head. “It wasn’t Holt. It was Terry. Jake came up on the Heartbreak Detector. We orchestrated a meet up between Jake and Amy and Terry decided to clip after about a minute and a half. He clipped them so Jake could be happy.”

Gina nodded in understanding. “That makes more sense. Of course it was Terry.”

“Terry loves love,” they both said in unison.

“Yeah,” Rosa agreed.

Gina took the envelope from Rosa. She weighed it in her hand. “So what? I’m supposed to help Jake acclimate to his new life as a human?”

Rosa shrugged. “That’s the unfair part.”

“You mean because I had to figure this out on my own? Just thrown from grace with no ideas of how to land on my feet?” Gina added bitterly.

Rosa broke eye contact and looked at her feet. “Yeah. Because of that.”

“Don’t worry. I’ll take care of Jake,” Gina assured. “I care about that little idiot too much to leave him hanging.”

Rosa looked back at her. “Thank you.”

“Can I say something unfair now?” Gina asked. Rosa nodded. With a sigh, Gina added, “I miss you.”

Rosa sighed to match Gina’s. “I miss you, too.” She looked around the sidewalk. “I should go. It was kind of chaos up there and I could sneak away. But they’ll notice soon enough. I can’t be here much longer.” Gina frowned. Rosa stepped forward quickly and wrapped her arms around Gina, enveloping her in a tight hug. Pulling away, she kissed Gina on the forehead. She grabbed her hand and squeezed it, making sure Gina held her eye contact. “Make good choices.”

Gina smiled through the tears springing in her eyes. “Yeah, you too. Or maybe don’t. You could get your wings clipped too. The three of us could form a club down here.”

Rosa released a dry laugh. “Don’t think I haven’t thought about it,” she answered, giving Gina’s hand one last squeeze before she released and walked away, disappearing into the night.

<3 <3

Jake walked nervously from the bar with Amy in tow. He turned to her on the sidewalk. She stepped into place in front of him. She was still wearing a contented expression.

“So, how would you feel about maybe going on an actual date sometime?” Jake asked. “Maybe tomorrow?”

“An actual date?” Amy questioned. “What would you call that?” she asked, gesturing back toward the bar.

“Just drinks. Would you really want to have gone on _two_ dates in one night?” Jake asked skeptically.

Amy laughed. “Oh you’re right. That makes me sound bad,” she agreed. “I can’t tomorrow because it’s Wednesday and I work late. But maybe the next day? Maybe Thursday?”

Jake stepped closer to Amy. “I think Thursday would work.” He couldn’t take his eyes off her. For the first time since he’d met her, he didn’t have to feel guilty for the way he felt for her. She stepped closer too. He looked down at her lips, ready to finally kiss her. The door to the bar opened and a group of loud people poured out, ruining the mood. Jake looked back at Amy. “So I will see you Thursday.”

Amy smiled brightly. “I can’t wait.” She hailed a cab and got inside. “I’ll see you then,” she said with a knowing smirk. Jake nodded before he closed the door and watched her be driven away.

He desperately wanted to go into planning mode for their date. He had to make sure their first official date was perfect. His life as a human depended on it. First though, he had to go to the address left for him. He had to assimilate into being a human.

He went to the address, walked up the stairs and knocked on the door. He waited anxiously for the door to be answered. He had no idea what was waiting for him on the other side. The door opened and Gina was standing there. “Hey, Kiddo. Welcome to Hell,” Gina said dryly.

“Excuse me?” Jake asked nervously.

“I’m kidding. I just really wanted to mess with you. Come on in,” Gina corrected, standing further back from the door to usher him in. “So you’re a human now?”

Jake shrugged. “That’s what I’ve been told. I don’t really know how it happened.”

“Terry and Rosa is how it happened,” Gina informed him. “They worked their Cupid magic and made you the charge this time.”

Jake nodded, piecing things together. “That would make sense,” he agreed. “Wait, how do you know all this?”

Gina sat down on the couch, patting the cushion next to her. “I had a visit from an old friend.”

“Terry?” Jake asked, still confused as to how Gina was so well informed.

“Not exactly,” Gina said blankly.

Suddenly it dawned on Jake. “Oh!” He cried. “Oh,” he added sedately. “Are you okay?”

Gina shrugged. “I’m fine.” Under Jake’s scrutinizing gaze, she caved. “I’m not _fine_ fine, but I’ll get there.”

Jake reached out and patted her shoulder. “I know you will.” Jake motioned to the envelope sitting in front of them. “So what’s this?”

Gina opened the envelope and poured out its contents. “It’s your basic welcome to human life package. Some might call it a severance package.” She motioned to the things on the table. “You got your phone, your birth certificate, a bank account with a small amount of savings, et cetera, et cetera. It’s basically all stuff to make up your life as a human. And not one who was recently made human.” She looked at Jake as he processed it all. “And we’re gonna have to find you a place to live. I can let you stay here for a while, but definitely not long term.”

Jake nodded, absorbing everything. His life as a cupid really was over. He felt sad that he’d never see Terry or Rosa or even Captain Holt again. But as he looked at Gina and as he thought of Amy, he realized he had a pretty promising life waiting for him as a human.

“Okay, Gina, consider this my boot camp,” Jake stated, rubbing his hands together. “Make me a human.”

<3 <3

It was a regular Wednesday morning for Amy. She got up at her normal time. She ate her normal breakfast. She got dressed and headed to the coffee shop at a normal time. Pretty much everything was normal except for one thing. She couldn’t wipe a smile off her face.

Running into Jake had been the best part of her day yesterday. She’d gone to the Stag’s Head because she wanted to forget her lame date. It had seemed so promising when Dave had asked her out, but then it just fell flat. She’d spent the whole date comparing Dave to Jake. And there was no comparison.

Jake was funnier. Jake was sweeter. Jake just made her feel happier than she had with Dave. She’d convinced herself she needed to forget Jake. And then boom, there he was. He looked just as shocked to see her as she was to see him. He quickly overcame his shock though and they fell into the same routine they’d always had. She may not have known Jake for very long, but she’d had a good feeling about him for a while now. When he asked her out on a date, she pretended to play coy. She really did work Wednesday but she didn’t want to seem too obvious. It was bad how far gone she was for Jake.

She walked into the coffee shop and spotted Jake sitting at their regular table. The smile she’d been unable to repress only grew in size. “Hi,” she greeted. He stood up, greeting her and holding out a drink. She grabbed it and took a sip. “You remembered my order?”

He shrugged, slightly blushing. “Eh, lucky guess.”

“Well thank you,” she replied. “It’s my favorite.” She took a deep breath and steeled herself. She may sound stupid, but she had something she really wanted to say. “It’s really good to see you here again.”

He got a look on his face that she couldn’t name. He moved quickly, wrapping one arm around her back and bringing her in for a kiss. He kissed her sweetly and quickly, pulling back far too soon for her liking.

“Sorry, I’ve just been wanting to do that for a while now,” he explained with a nervous grin. “Kinda since you spilled your coffee on me.”

Amy laughed at the memory. She put her coffee down on the table next to them. “Yeah, I know the feeling.” She reached up and pulled him back in for another kiss. This time was even better. He wrapped his arm back around her, kissing her deeply. She reciprocated equally, putting all the feelings she had into the kiss. She heard someone clear their throat near them. They broke apart with guilty looks on both their faces.

Jake left his arm wrapped around Amy. “Maybe this is an inappropriate place for that,” he said nervously.

She chuckled in reply, playing with the hair at his neck. “I don’t have to be at work for a few more hours. We could go somewhere else.”

Jake looked like he was thinking things over. “There’s a park nearby…”

Amy pulled her hand back and smacked his shoulder excitedly. “There _is_ a park nearby!” Jake looked confused but excited by her reaction. “Let’s go!” She cheered, grabbing her cup off the table.

They walked out of the coffee shop, holding hands. They walked down the sidewalk toward the nearby park. Amy weighed the risks of saying something too forward. She decided to go for it. So far it had worked out in her favor. “I’m really glad you showed up today,” Amy stated, looking over at him. “I’m glad our Wednesday dates have been reinstated.”

Jake looked over at her and smiled broadly. He gave her hand a squeeze. “There’s literally nowhere I’d rather be.”

**Notes for the Chapter:**

> Today has been a long day! I drove 5 and a half hours, plotting this in my head, wanting so badly to get it down before I forgot parts I wanted to include. So I got home and grabbed my computer and went crazy. I hope you liked it!
> 
> Fun fact: The Stag's Head is a real bar. It's not in New York. It's a pub I went to when I was studying abroad in England. I thought it would be fun to throw it in there. 
> 
> Thank you, thank you, thank you for reading and leaving comments and kudos! They truly make my day! I love hearing what you guys think of the chapters! 
> 
> I expect to have one more chapter! For some reason, I can't ever end without an epilogue. So we still have that to look forward to!


	7. We've Got Our Love to Pay the Bills

ONE YEAR LATER

Jake thought he’d done a pretty good job adjusting to human life over the last year. He’d had Gina’s coaching skills which sometimes were more painful than he had anticipated. He had a tiny apartment that he was happy with. Amy had gotten him a job at the precinct. He was the civilian administrator for the third floor. So basically he and Gina did the same job, he just was on a different floor. He was happy with it though. He got to see Amy even when she was ridiculously busy. He made friends at the precinct rather quickly. Charles Boyle had become his friend pretty quickly. Jake had to pretend like he didn’t already know so much about his life. It was a good thing Charles shared so much so fast. Jake didn’t have to pretend for too long.

He and Amy were happy. Like really happy. Jake had spent years watching other people be blissfully happy. He’d never expected to find this himself. And yet he did. With Amy, who was even more wonderful than Jake could have imagined. It was kind of ridiculous how in love with her he was. He’d known some really awesome people in his life, but no one could hold a candle to Amy. She was the love of his life and he finally got to share his life with her.

They were taking things at a slow pace. Sure he’d told her that he loved her, but otherwise, things were moving at a comfortable pace. Yes, they saw each other literally every day, but that was work related. The point was that they were happy and Jake was relieved that he hadn’t given up his life as a cupid to be unhappy.

He did miss being a cupid sometimes. He missed Rosa and Terry and, oddly enough, Holt. He missed the cool things he got to do as a cupid. His job as a cupid was certainly more fulfilling than his job as a civilian administrator. He sometimes would try to set up the people in the precinct. He got two cops to go on a date once and he felt a small victory. He had no idea where it went from there, but he was proud of himself for still having the skills.

^^

The strangest change came four months after Jake had become human. There was one day he was sitting at his desk, typing up some report when someone walked up to his desk and kicked the side of it. He was startled and turned toward the noise. He froze in his chair, his eyes growing wide. “Rosa?” He asked, confused and worried.

“Hey,” she said with no further explanation.

“What are you doing here?”

“Things are changing. I wanted to talk to you about it,” Rosa explained.

“Okay,” Jake said, gesturing to a chair by his desk. “Let’s talk.”

“Not here.”

Jake rolled his eyes. “Seriously?” She nodded. “Well where?”

“Go to that bar where you got your wings clipped. I’ll be there around 7:00,” Rosa ordered.

“7:00?” Jake asked hesitantly. “Amy and I kinda had dinner plans around that time…” Rosa glared at him. “But I will obviously reschedule those.”

“Be there and tell no one,” Rosa demanded. Jake nodded and she turned and walked away. Jake sat there stunned for a few minutes before he went one floor up to find Amy.

“Hey, Babe!” He cheered, walking into the break room.

“Hey!” She replied happily. “What brings you up to the fourth floor?”

“It’s about tonight,” Jake said hesitantly. “I kinda…have to cancel.” Amy’s face dropped. “But I promise tomorrow night we can go to that restaurant. I’m sorry. Something just came up.”

“Something came up?” Amy asked skeptically.

“Look, I can explain some time when Gina isn’t in earshot,” Jake conceded.

“Promise?”

Jake smiled, leaning in and kissing her quickly on the cheek. “Cross my heart!”

Amy sighed, a small smile on her face. “Okay, I guess you’re off the hook. Why don’t you come by my place whenever you’re done with…whatever it is you’re doing?”

Jake smiled broadly and nodded. “I like that plan.” He started to walk out and he turned back to her quickly. “Thanks for being so cool.”

Amy held up her arms. “That’s what I’m known for. Being cool!”

Gina walked in laughing. “Yeah, sure, Ames. _That’s_ what you’re known for. Okay,” Gina replied, her comments dripping in sarcasm. Amy glared at her. Gina turned to Jake. “Why have you abandoned your post?”

“Going back now. Just, uh, wanted to see my lady,” Jake sort of lied.

Gina scrunched up her face in disgust. “I hate you two together. Honestly. You’re just the grossest.”

Amy and Jake looked at each other and shook their heads, walking from the break room together. Amy grabbed and squeezed Jake’s hand quickly. “See you tonight!”

“Can’t wait!” Jake cheered back as he walked toward the stairs.

Jake waited at the Stag’s Head for five minutes before Rosa walked in. He had a beer waiting for her. She sat down next to him, not really acknowledging him or the drink. She just sat there.

“So are you going to tell me why you’re being so cryptic?” Jake asked.

Finally she looked over at him. Her face was filled with concern. “Things are…changing…in my world.” Jake nodded for her to continue. “Terry’s been urging Captain Holt to be more lax with the cupid rules. And today he declared that our previous limits for humanizing are gone. We have the ability to interact with the human world at will. He doesn’t necessarily advise it, but he isn’t limiting us anymore.”

“Why?” Jake asked, taking a sip of his beer.

“Because we lost one of the best due to the damn rules,” Rosa begrudgingly admitted.

Jake placed his hand over his heart, a huge grin emerging on his face. “I am so touched, Rosa.”

“Shut up.”

“No really, it’s like I guess sometimes you have to leave somewhere to know how much you really meant to it,” Jake said dreamily.

Rosa glared at him. “You know precisely how important you were. Don’t act like you’re surprised.”

Jake smirked with a shrug. “I guess so. I just didn’t imagine something like this would happen. So what are these changes?”

“Basically, they don’t want another incident where you fell in love with a human and quit. So they aren’t being strict on humanizing anymore,” Rosa elaborated.

Jake felt confused. “Okay? That sounds great. What’s so wrong about it?”

Rosa sighed. “I said some pretty dumb things when Gina got her wings clipped. Because it was easier for me. I don’t know how to tell her this. What if she doesn’t want me around now that I actually could be?”

Jake gaped at her. “Hold up! You’re coming to me for relationship advice? God, this day is just getting better and better!” Rosa punched Jake on the arm. “Ow! Okay, okay, calm down.” Jake turned and looked Rosa in the eye. “She misses you. I’m sure if you just apologized, she’d be fine. I’m sure she’d be happy to see you. And happy to know that she can continue to see you. She was a little messed up after she saw you the last time, but if there isn’t a rule about it anymore, then everything should be fine. Right?”

Rosa looked like she was thinking things through. “I guess.” She took a long draw from her beer. “I just don’t know how to approach her.”

“Look, when I ghosted on Amy because everyone told me I had to, I hated it. You know that. And then when we ran into each other again, I just laid it all out there. It was important to me to salvage my relationship with Amy so I put my heart on the line and asked her to forgive me for not being there. I think you had a pretty good reason for not being there, Rosa. It was against the rules,” Jake reminded her.

She looked like she was thinking about what he said. “Yeah. But I didn’t have to be a dick to her when she was leaving.”

Jake scoffed. “Please, everyone, especially Gina, knows you lash out when you’re scared.”

Rosa glared at him. “Excuse me?”

Jake nodded confidently. “Remember when you were freaking out about that final exam at the academy? You lashed out at me hard! You told me my hair was stupid and that if I continued to act like such a child, I’d never get anywhere in life where someone respected me,” Jake recalled.

Rosa stared at him in disbelief. “Wow. You held on to that for a long time.”

Jake laughed. “Well you wounded me, Rosa.” Rosa shook her head and laughed lightly. “Just talk to her,” Jake urged. Rosa looked up at him nervously. “And if you want some buffers, Amy and I can be there!”

“Is this just what you do? Bring up Amy needlessly in conversation?” Rosa asked bluntly.

“You could talk to Gina about how annoying I am about Amy. I’m sure you guys would bond over that really well. She’d forget all the terrible things you said to her,” Jake offered.

Rosa nodded thoughtfully. Jake could tell she had a lot on her mind. Finally she looked over at him. “Thanks, Jake. I think I might take your advice.”

“I hope you do. I should go. I promised Amy I’d stop by tonight in lieu of our date,” He said, standing up and laying money down on the table.

“I’d like to meet her some time,” Rosa said, looking up at Jake. “I’ve heard so much about her. It would be nice to actually know her.”

“She’s pretty great,” Jake gushed. “Maybe if you’re hanging out in the real world more, you can get to know her.” Rosa nodded. “Good seeing you, Diaz.”

“Good seeing you too, Peralta.”

Jake smiled. He pointed his finger at Rosa. “Now go win your lady back. And that’s an order.”

^^

Rosa had slowly become a part of their lives again. Gina had of course really made her work for it. Jake expected nothing less. Times when she was less busy, Rosa spent lots of time with them. They had to lie to Amy about where it was that Rosa went. But all the lies left Jake feeling uneasy. It got him thinking.

“So you’re gonna tell her?” Gina asked Jake as they sat in her apartment watching TV one afternoon.

“Yeah, I think I am,” Jake replied. “I mean, we’ve been together for a year. I should tell her.”

Gina looked over at him skeptically. “She’s not going to believe you.”

“Why?”

“She’s a detective. She’s going to want proof,” Gina countered.

“I think it’ll be okay,” Jake added optimistically.

“I see it going terribly,” Rosa added, walking in the room and sitting down between Jake and Gina on the couch.

“Well I wasn’t asking you. I was asking Gina,” Jake replied quickly.

“I, too, think it’ll go terribly,” Gina confirmed with a grin, interlocking her hand with Rosa’s.

“You guys suck. It’s so much better when it’s the four of us and you two can’t gang up on me,” Jake whined, standing up and heading toward the door.

“Look, Jake,” Rosa started. Jake turned around and looked at her. “You gave up everything for her. Your whole life. What if you tell her the truth and she thinks you’re a freak and she leaves you because of it? Is it really that hard to just be vague about it? Is it worth losing her over?”

Jake looked at her. “If she can’t handle me being honest about my past, then it wouldn’t be love in the first place. If one little detail about myself is going to drive her away, it wasn’t that strong to begin with,” Jake argued. “But it _is_ love and we _are_ strong. And I think it’ll be fine.”

“Your call, girl, but you know there’s no regrowing wings. Once they’re clipped, they’re clipped,” Gina reminded him. “Or did that change too?” She asked Rosa. Rosa shook her head.

“It’ll be fine,” Jake assured them. Of course, he was also assuring himself.

^^

Amy met Jake at his apartment after she got off work. Jake was a pile of nerves. He was determined to tell Amy the truth, but Gina and Rosa scared him. He couldn’t lose Amy. She was so important to him. He had friends, but nothing in the human world compared to Amy. He’d given up his cupid life for her. What if she really left him over the truth?

She was wandering around his apartment, changing into some casual clothes of hers that she kept there. She walked in and plopped down on the couch next to Jake. Being next to her calmed him some, but not much. He turned to her slowly.

“Ames, can I talk to you about something?” He asked, fighting a voice break.

She nodded absentmindedly. “Of course, Babe.”

“It’s something big,” he added.

She looked curious. She set down her phone and looked at him. She almost looked concerned. “Are you leaving me?”

Jake shook his head vehemently. “God, no!” Relief swept over her demeanor. “Amy, I love you.”

She smiled. “I love you, too.”

“I just wanted to come clean about something,” Jake admitted. She looked concerned again. “Wow, there’s really no good way to lead into this.” He rubbed his hands together and sighed.

“Look, Amy, when we met, I wasn’t entirely honest about who I was,” he was trying to formulate his thoughts quickly to get the concern off her face.

“Are you married?” Amy demanded.

“Not at all,” Jake promised. “I just wasn’t exactly who I said I was. I said I worked for an internet dating site, but that wasn’t true.” He paused.

“Jake, please don’t confess to anything illegal. I really don’t want to have to arrest you,” Amy pleaded.

“It’s not illegal. It’s just hard to believe.” Amy stared at him. “When we met the first time in the coffee shop, and every time after until we got drinks in the bar…I was…a cupid.”

“A cupid?” Amy asked incredulously.

Jake closed his eyes. He could feel her doubt. “Yes. I used to be a cupid. An angel of love. My job was to find perfect matches and set them up. I was really good at it too. Until…” he faltered.

“Until?”

“Until you,” he said, his eyes still closed. He sighed, finally looking at Amy. “I had probably thousands of charges over the years that I was a cupid and the last charge I ever had was…you.”

“I was your charge?” Amy asked.

Jake nodded. “So here’s what happened. I was a cupid. I was really good at it. And then I got your case and I didn’t feel like I knew enough to find your perfect match. So I “humanized” so I could meet you and try to figure out what would be perfect for you. The problem was once I met you, I…really liked you.” He sighed. “So I kept becoming human so that I could see you even though it broke all the rules. But I didn’t care because I enjoyed spending time with you so much. And it was ridiculous and I almost lost my wings over it. And I just decided to do my job and find you your perfect match. And I thought I had, but when you found me at the bar I was supposed to be invisible but I wasn’t because my wings had been clipped.” Jake sped through his explanation, taking a deep breath at the end.

He looked over at Amy, afraid of her reaction. She looked deep in thought. He covered his face. “Look, I know this makes me sound like a total creep or something. So I’m just going to cover my eyes and you are free to leave. I get it. I’m weird. So you just go and don’t feel bad about it. We had a good run. Just go and don’t worry about seeing my devastated face when you leave.”

Jake held his hands over his face. He didn’t feel any movement on the couch. He didn’t hear the door. But he also didn’t know how Amy was taking any of the information he’d just spouted.

“Did you set me up with my aunt’s dentist?” Amy asked, still next to him.

He uncovered his face and looked over at her in awe. “You’re still here,” he said softly.

She looked at him like he was crazy. “Yes, I’m still here. But answer my question.”

He looked down at his hands guiltily, “Yeah, I did.” He heard her gasp. He looked up at her. “I was catching heat for not having set you up with anyone and I was buying myself some time to still see you and so I sent you a crappy date. I’m sorry. Truly.” Amy laughed. Jake was confused. “Are you laughing?” She nodded.

He reached out and grabbed her hand. “You know, you’re taking this a lot better than I expected.”

“What did you expect me to do? Run away?” Amy questioned.

Jake nodded slightly. “Maybe a little. I mean, it’s kinda weird, don’t you think? Humans don’t even know cupids exist.”

“Maybe not, but I believe you,” Amy maintained.

Jake shook his head disbelievingly. “But why?”

“Because you have no reason to lie to me,” Amy replied with a smile. “You were afraid that what you had to tell me would drive me away. Why would you come up with some weird elaborate story for a lie?”

“Wow,” Jake said, genuinely in awe. “You’re amazing.”

Amy smiled brightly. “I know.” She looked thoughtful suddenly. “Wait a minute.”

Jake was concerned again.

“You said you were a cupid up until we started dating, right?” Jake nodded. “But you knew Gina when I brought you to the precinct before that.” She paused. Jake could see the gears turning. She turned to him suddenly with a gasp. “Was Gina a cupid?”

Jake froze. He didn’t know if he should admit everything. Quickly he gave in. If he was sharing secrets, why keep certain things secrets? He nodded. “Yeah, she was.” Amy laughed to herself, pumping her fist in the air. “We knew each other because we grew up together. She was one of the people that told me I had to stop seeing you.”

Amy gaped at him. “How rude of her.”

Jake laughed. “She was just trying to protect me. From losing my job.”

“But you did anyway,” Amy reminded him. She got a sad look on her face. “Jake, did I make you lose your job?”

Jake shook his head. “No!” Amy looked unsure. “I got an honorable clipping. They released me from my duties. I wasn’t fired. They decided to let me pursue my feelings so I could be happy rather than keep me as a cupid.”

“So you lost your job because of me?” Amy repeated.

“No, it wasn’t because of you it was…I don’t know, _for_ you. So I could be with you,” Jake explained weakly.

Amy was processing. She giggled to herself. “What if I didn’t like you back?”

Jake laughed. “Yeah, believe me, I was worried about that!”

Amy laughed loudly, leaning forward and laying her head on Jake’s shoulder. “That’s crazy talk.” She picked her head up and looked him in the eye. “I was just as crazy about you. I’d probably have done the same things.”

Jake smiled happily. “Seriously?”

Amy leaned in and kissed him sweetly. She pulled back with her hands cupping the sides of his face. “Seriously.” She paused for a moment. “You know I want to know more, right?”

Jake chuckled. “I should have suspected. Lay it on me.”

Amy grinned. “So did Gina have an honorable clipping or whatever too?”

Jake grimaced. “Not exactly. She was more dramatic with her pairings and sometimes they ended up in the hospital.” Amy looked only mildly shocked. “Any other questions?”

“So who are some other people you’ve matched?”

Jake looked at her for a moment. “You know Charles and Genevieve?”

Amy shot him a look. “You mean your new best friend Charles and his girlfriend that he never shuts up about? Yes, I’m familiar with them.”

Jake nodded. “Yeah, I did that.”

Amy smiled at him. “I guess you do have a gift. As much over-sharing a Charles does now, he’s still way more tolerable than before Genevieve.” Amy thought for a moment more. “Plus they're adopting a kid. They’re becoming a family.” She turned to Jake. “You did that. That’s awesome.” Jake smiled happily, settling back into the couch. Amy sunk down with him, wrapping herself against him.

They sat there in a comfortable silence for a few minutes. Jake just felt relieved that Amy was being so cool.

“So did you guys have a uniform or something as cupids?” Amy asked, breaking the silence.

Jake sat forward and looked at her blankly. “I know where this is going and no I didn’t wear a diaper.” Amy laid back on the couch laughing hysterically. Jake shook his head, laughing at how hard she was laughing. “I said I _didn’t_ wear a diaper,” he clarified.

Amy caught her breath. “I know, but I still pictured it. It looks really good Jake.”

“I’m not doing it, Santiago.”

“What about Halloween?” Amy asked, doing her best puppy dog eyes.

Jake sighed. “You’re going to somehow talk me into this, aren’t you?” Amy smirked devilishly and nodded. “You’re the worst.”

“Nuh-uh,” Amy disagreed. “You love me.”

“I can still love you even if you’re the worst,” Jake argued.

They sat there in silence a while longer, Amy clearly plotting in her head. Jake reached over and grabbed her hand. He pulled her hand up to his mouth and laid a kiss on it. She smiled at him. “Thank you,” he said simply.

“For?”

He shrugged. “I don’t know, for being wonderful. For believing me. For accepting me. For loving me anyway,” he replied.

She scooted closer to him on the couch and curled her body around his. “You’d do the same for me. That’s why we’re the perfect match,” she said with a smile. She looked at him closely for a second. “Is that the right terminology?”

Jake laughed and nodded. They sat curled around each other, absorbing each other’s presence for a while until Gina waked unannounced into Jake’s apartment. She wandered in, walked to the kitchen and got herself a drink and walked back toward the living room. She said nothing to them.

“Hey, Cupid!” Amy greeted.

Gina looked at her with no humor on her face. She looked over at Jake. “So you told her?” Jake nodded. “And she’s still here. Well I guess you know better than Rosa and I.”

“Rosa!” Amy yelled suddenly. “Did she used to be a cupid too?”

Gina shook her head. “Nah, she still is a cupid.”

“What?” Amy asked, confused. She turned to Jake. “I thought you said you couldn’t have human interaction?”

Jake opened his mouth to speak but Gina beat him to it. “Turns out when the prince leaves, rules get changed.”

“Oh come on, I wasn’t the prince,” Jake argued. Gina shook her head in disagreement. “Whatever. If it wasn’t for the rules changing you wouldn’t have your girlfriend back. You wouldn’t be all gross.”

“We’re not as gross as you two,” Gina demanded.

“I don’t know,” Jake argued. “You guys can be a pretty gross couple.”  Gina and Jake were just gearing up.

“You know, I gotta say, your lie about your job was pretty good,” Amy interjected, changing the subject. “A fake dating web site. That’s pretty good.” Jake smirked smugly. “You guys should really do that,” Amy decided.

“What?” Gina asked.

“You guys should make your own dating site. You said you could still make matches. Jake set up those cops down on the third floor,” Amy reminded them. “You should do it. You could still do what you loved. You can help people find love.”

Jake and Gina looked at each other like an idea was sparking. They both started nodding slowly. Jake could see the gears turning in Gina’s head same as they were in his. It would be fun to try it and see how many matches they could still make.

“Holt would be so pissed,” Gina said.

“Rosa will call us both idiots,” Jake added.

Gina grinned. “We should do it.”

“I’ve already got the perfect name,” Jake exclaimed.

“Angel of Love!” They said in unison. They looked at each other excitedly.

Gina turned to Amy. “This might be the best idea you’ve ever had, Santiago.”

“I believe in you guys,” Amy affirmed. She curled her arm around Jake’s, laying her head on his shoulder. Jake laid a kiss on the crown of her head. “After all, I had the best cupid around.”

**Notes for the Chapter:**

> And that's it folks!  
> Thank you so much to Erica (startofamoment) for letting me take this beautiful AU she made and write a whole fic about it! Thanks for trusting me with your story!  
> Thank you to everyone who left me comments and kudos and encouraged me to keep writing. This was the most I've had to do to set up a universe so I appreciate you guys sticking with me!  
> Thank you so much for reading!  
> I hope you all enjoyed this!

**Author's Note:**

> Please let me know what you thought! I'm excited to write this one. It's very different from what I've written in the past but I can't wait to keep writing on it!  
> Feel free to come chat with me on tumblr. I'm three-drink-amy! (this was recently changed) I'd love to hear from you!


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